


The Decisions and Firsts of Ryan Howard

by cc tinslebee (Doitlikeagreaser)



Series: The Redemption of Ryan Howard [1]
Category: The Office (US)
Genre: 5+1 Things, Angst with a Happy Ending, Bisexual Male Character, Canon Compliant, Character Study, Commitment, F/M, Fix-It, Implied Sexual Content, Implied/Referenced Drug Use, M/M, Multi, Non-Canon Relationship, Non-Consensual Drug Use, Peer Pressure, Pining, Polyamorous Character, Ryan-centric, Self-Destructive Behavior, Temporarily Unrequited Love, The Michael Scott Paper Company
Language: English
Status: Completed
Published: 2020-03-25
Updated: 2020-03-25
Packaged: 2021-03-01 02:35:37
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 6
Words: 9,335
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23147860
Author URL: https://archiveofourown.org/users/Doitlikeagreaser/pseuds/cc%20tinslebee
Summary: Ryan Howard didn't have the best track record for decisions and the things he has decided in his own mind were no different. These are five times he made an important decision in his mind and one time it changed him for the better.
Relationships: Jim Halpert/Ryan Howard, Pam Beesly/Jim Halpert, Pam Beesly/Jim Halpert/Ryan Howard, Pam Beesly/Ryan Howard, Ryan Howard & Drake Howard, Ryan Howard & Oscar Martinez, Ryan Howard/Kelly Kapoor
Series: The Redemption of Ryan Howard [1]
Series URL: https://archiveofourown.org/series/1674481
Comments: 10
Kudos: 46





	1. Kelly Kapoor

  1. When Ryan first decides he’s going to stay with Kelly Kapoor, he knows he has no other option.



He was talking to Pam in the kitchen, because _that’s_ something he’s been doing recently. Talking to Pam, that is. Pam's nice and easy to talk to; he really, truly gets why Jim liked her so much. Things with Pam are just so much easier and natural than they’ll ever be with Kelly, he thinks. 

“I guess some new people might be coming from Stamford,” Pam stated as she dipped her tea bag into her mug. “Should be fun. New blood.”

“Is Jim coming back?” he replied carefully. He guessed that it might be an open wound for her still, but his curiosity gets the best of him.

“That’s, um--I hadn’t thought about that,” she told him (you know, like a liar). “I don’t know. Huh.”

“I just don’t want it to be weird,” he admitted. “You know?”

She nods slightly, but he quickly picks up on the panicked look on her face.

“I mean, I took his old job and his old desk,” he clarified, acting oblivious.

“Yeah, yeah, that might be weird,” Pam submitted.

Ryan started to move over to the refrigerator when Pam spoke again. “Overall, though, we still all have our jobs, so good news, right?” she said positively as she turned to look at him.

“Oh, yeah,” Ryan agreed genuinely as he opened the refrigerator door and reached in, “Totally.”

Suddenly, Kelly ran into the room screaming as she tackled Ryan into the fridge, nearly taking his arm off in the process. She wrapped her arms around his neck in a hysterical hug, “I’m so happy! We don’t have to break up now, Ryan!”

He couldn’t help but wrap his arms around her waist as she peppered his face with kisses. Ryan could almost feel the camera zoom in on his face as he looked directly at the lense, defeated, but not completely unhappy.

“This is the best day of my whole life!” she squealed and Pam waved to Ryan as she headed out. 

The camera crew saved him from any further affectionate assaults from Kelly and into their own integration. They ask him the same question he asks himself: Why didn’t he just come clean and break up with her?

“I don’t know,” Ryan tells them honestly. He looks defeated at first, but a faint smile is tugging at his lips. “I can’t explain it.” He finally looks at them, his expression a mixture of seemingly amustion and questionably fondness.

It’s not as though he feels obligated to spare her from heartbreak -- but _God_ , he’s not inclined to make the poor girl cry or anything. It’s not as though he feels trapped in the relationship either. Well, in a way he does, but that’s not his motivation for staying with her. Ryan wasn't blind; he noticed the signs of manipulation on both of their ends earlier on in the relationship. He may not of known it for sure, but he had suspected that if this relationship continued, they wouldn't stop blatantly manipulating each other. Kelly was desperate to keep him and Ryan was determined to keep her at an arms length. He knew that even if they could, they wouldn't break the cycle. If he had ever gotten the chance again, he would break up with her for good. 

In truth, Ryan actually didn’t mind Kelly that much. There were these little moments now and then when she would just quiet down -- either from burning herself out or some other reason -- and it was those moments where Ryan felt as though he could really appreciate her. Ryan liked it especially when she talked about something _real_ , something legitimate that he could get behind. Those were the times where he could safely say that her passion wasn’t entirely misplaced.

He wasn’t in the relationship to use her or be used by her either. He didn’t exactly mind the fact that they slept together, but despite it being the founding reason for their relationship, it wasn’t the main purpose of it. He wasn’t even sure what the main purpose even was, he just considered sleeping together to be a perk rather than a main focus.

Kelly was a loud night, though, which wasn’t surprising. For one, when _wasn’t_ Kelly loud? For the other, Ryan understood from personal experience that it's not something that’s easily avoidable in that situation. (Ryan wasn’t a fool; he had experimented in college, and in high school… and in adult life. He could barely call it ‘experimenting’ anymore, because at this point, he knew what he liked and he stuck with it. ‘What he liked’ just happened to be both.)

Despite this, Kelly was also extremely vanilla; which is fine, but there’s only so much of topping _and_ vanilla that Ryan could take. And Ryan was beyond fine with the excessive vanilla part, but despite it being so in-character for Kelly’s white-picket-fence personality, it just felt _wrong_ to him. Like he and Kelly both deserved to do that exclusively with respective people that they loved like that. Which is a delicate way of saying that wasn’t each other.

Ryan thought that in another life, they might have been able to be the type of friends that talked about their lives, gossiped about the people around them, and facetiously called each other ‘babe.’ He would have liked that; Ryan thought he might have been able to pull off being Kelly’s gay-best-friend in another life. Unfortunately, that just wasn’t for the _them_ here and now.

Ryan knew he would never be able to give Kelly the perfect marriage and life that she wanted and deserved. He just couldn’t _commit_ like she wanted him to. He wondered if he would ever be able to commit to an idea or person like most reasonable people wanted. Ryan just didn’t feel as though that was made for him.

For now, he would indulge Kelly a little more. Maybe one day things would change. 

When Ryan first made the decision to continue dating Kelly Kapoor, he made the decision consciously and not out of obligation. She needed somebody and so did he; it was as simple as that.

**Notes for the Chapter:**

> Episode Referenced:  
> Branch Closing


	2. Troy Underbridge

**Notes for the Chapter:**

> Trigger Warning: This part talks about the non-consensual administration of a drug and also some dubious consent. It's not gone into detail, but I wanted to just give a quick heads up.

2\. When Ryan first gets into the drug game, he’s sad and lonely and has a _lot_ of newfound wealth to blow it on.

He’s in New York City as a corporate hotshot, he’s a fresh face in the world of Dunder Mifflin with new ideas, and he is _so_ much better than Jan Levinson. 

On the downside, he’s never felt so depressed and touch-starved in all of his life, he’s miles from home and anything familiar, and he broke up with Kelly weeks ago. To top it all off, he couldn't help but imagine unprompted how perfect life must be going for Jim Halpert and Pam Beesly right about now.

And it was definitely _not_ the result of Pam rejecting him on his last visit to Scranton.

He didn’t even know why he did it; the newfound confidence had really gotten to his head that day and he figured ‘Why the hell not?’ Famous last words, he supposed. Of _course_ she’s dating Jim now. 

Ryan couldn’t entirely blame this on Pam’s rejection alone or call it the final push. This was a long time coming and Ryan knew it. 

But there he was in a nightclub in New York, surrounded by coworkers he really didn’t care about and in an atmosphere that made him sick to the core. That was just the New York City lifestyle for you. Ryan yearned for the days where there was only one party he didn’t want to be at.

Somewhere through the haze that was an absurd amount of people in such a tiny area and loud, obnoxious music that he’s supposed to like as a young Millennial, Troy Underbridge approached him.

“Having fun, pal?” he yelled over the obscenely loud music. 

“Not really,” Ryan yelled back, taking a sip of his drink out of boredom.

“Boy, do I have the thing for you!” Troy shouted, reaching into his jacket pocket for something. When his hand emerged from the coat, Ryan catched the glimpse of a small, plastic bag with white powder.

“What the hell is that?” Ryan asked.

“This,” Troy relished, gingerly placing the bag in the palm of Ryan’s hand discreetly, “is the stuff you need to have a good time.”

Ryan looked numbly at the small bag in his hand. His heart hammered and he began to shake for a reason he couldn't explain.

“So, what do you say?” Troy asked smoothly and Ryan knew that he was a goner.

Before Ryan could even respond, Troy took his drink from his hands and put it to Ryan’s mouth, making him down the last of the glass. Troy then put it on the nearest counter and led Ryan outside.

It all had happened so fast, Ryan didn’t even register, let alone remember, how Troy had administered the drug. He only remembered that one moment, he was outside and the next, he was back inside the sweaty club already high as a kite.

Troy led him around the club for what seemed like hours, settling him in the center of the booming crowd and at the bar where he consumed even more alcohol. Some girls flirted with him, some guys too. They touched his hair, his arm, his thigh. He didn’t do anything to stop them, but in the end, Troy would pull him away from them and back into the center of the room. When Troy pulled him back to the bar, whoever had been there was gone and replaced with someone new. Ryan thought that saving him from those random people was the least he could do considering he just _drugged_ him.

Somewhere along the line, Troy had ditched him. In a moment of abandonment, Ryan had thought that he was going to die there like that. He didn’t want to, but he felt as though he might have deserved it. One of his favorite movie stars, River Phoenix certainly didn’t _deserve_ to die that way either, but fate is a cruel mistress. 

It wasn’t until an attractive stranger sent a well-needed glass of water his way that he thought things were looking up. He decided that things were still looking up when said stranger was kissing him up against a wall and he didn’t mind it one bit. Even if the wall was a part of the same alleyway Troy doped him up in.

Ryan couldn’t help but passingly wonder if Meredith had ever been in a similar situation. He chuckled through his buzzed state at the irony.

The next day, Ryan woke up with a killer hangover, blinding light peeking through his apartment’s windows, and a person of undetermined gender sleeping soundly beside him. Though, by the way his legs ached as he attempted to walk, he could take a guess.

He also tried to ignore the nagging thought that the person in his bed resembled Jim Halpert.

The hangover alone made him want to hit his head against the wall of his small apartment. There was no way he was going into work today and there was no way he could face whoever it was that he had brought into his apartment. Instead, he made sure he had all of his keys, left a cup of coffee for the person in his bed and a note telling them how much he had appreciated their kindness to him last night, but kindly requesting that they leave by the time he got back. From where, he never said.

The first time Ryan made the decision to do drugs, it was not the decision that he made. The second and third time, however, was a different story.

**Notes for the Chapter:**

> Episode Referenced:  
> Night Out


	3. Jim Halpert

3\. The first time Ryan finds out that he’s in love with Jim Halpert, he catches Jim staring at him at the reception desk.

He was just minding his own business, doing the one job he was supposed to be doing when by chance he looked up at the exact same time Jim was staring at him. He ceased his typing and his eyes dodged from his left to his right before finally settling on Jim. “What?” he said, almost amused.

Jim looked equally as shocked to be caught. “Oh, nothing,” he dismissed, trying to act nonchalant.

Ryan returned to his work, almost disappointed that this ‘nothing’ distracted him from the task at hand.

It wasn’t long before Jim’s eyes drifted to Ryan’s direction once again. A phone rang in the office causing Ryan to look up and meet his gaze again. “What?” he repeated, too amused at the situation to actually be mad.

Jim, once again caught in the act, tried to play it off, “Oh, nothing.”

Ryan shook his head at the pure ridiculousness of it all and returned to his work, unsure of what else he could do.

Truth be told, Ryan actually kind of enjoyed the attention. It was nice getting attention from a nice, good-looking co-worker -- more importantly a co-worker that was _not_ Michael Scott -- and he didn’t really care at the moment if the attention was misplaced. Ryan knew that Jim only looks at him thinking he’ll see Pam, but he doesn’t look away when Ryan’s the one he sees.

Ryan could live with that.

“Jim’s been looking at me kind of a lot all week. I would be creeped out by it, but it’s nothing compared to the way Michael looks at me,” Ryan told the cameras instead. He pulled his arms closer together out of uncomfort because on the other hand, Michael’s staring _did_ make him uncomfortable.

It was more like Ryan fell for Jim in that moment more than anything. In truth, he hadn’t even realised it until much later. Almost several years later at that.

Ryan was sitting with Meredith and Kelly one day on their lunch break. When he noticed Jim heading their way, he quickly sat up in anticipation.

“Hey, Ryan, could you start consolidating all of our rolodex information into outlook?” Jim-the-co-manager asked him. Ryan almost laughed at the irony; he used to be a big corporate hotshot who took pleasure out of bossing Jim around and now look at how the tables had turned. 

Ryan decided to mess with him. “Uh, it doesn’t seem like there’s much of a point if the company’s going under.”

“But if the company doesn’t go under, then we’ll finally have all our contacts in one program,” Jim argued goodnaturedly.

“The company’s probably probably going under though,” Ryan replied with a smirk.

“It could go either way,” Jim said quickly.

“Seems like it’s leaning one way,” Ryan countered.

“Maybe we should just wait and find out,” Jim settled.

Ryan agreed, “Definitely.”

“Okay,” Jim said with relief. He began to turn around.

“So should we wait to find out before we start doing all this?” Ryan added like the smartass he was.

“Nah, might as well do it now,” Jim replied in an equally smartass way.

Jim gave him one of those closed-lip smiles and he left the room with ease, leaving Ryan somewhat dumbfounded. Kelly noticed, but didn’t comment about how his mouth sort of hung open. She continued to engage Meredith in conversation.

It’s not like Jim had said anything out of character for him. It was the opposite, actually. That might have been what had done him in. Ryan was always a person who was attracted to good leaders; he wanted to be _led_ (but, like, only when he was in the mood to be led, you know?). With Jim suddenly challenging him, it sent Ryan back to the day when he caught Jim staring at him searching for Pam. He realised for the first time with sudden clarity that _Oh shit, I’m in love with that lanky idiot_.

Kelly nudged Ryan out of his thoughts. "Hey, Meredith, did you know that since Jim only handles the day-to-day stuff as co-manager, he doesn't have as much power as Michael does?"

"Really?" Meredith asked, leaning forward, intrigued.

"That's right. He can't fire people either; Ryan told me. Isn't that right, babe?" Kelly looked to him.

Ryan recognized a good old Kelly rumor when he saw one. "Yeah, totally."

Ryan gave Kelly permission to spread the rumor while he continued to ponder about his dilemna throughout the day, while simultaneously pushing his luck with Jim. He even took a generous break during Creed’s lunch slot to talk to him about various things, including the older man’s newfound takenness with Ronni, the new receptionist. 

“Do you love her, or do you love the idea of her?” Ryan asked in a faux-philosophical tone while trying to juggle a ball, though he knew he was thinking out loud himself.

“I don’t know, man,” replied Creed, shaking his head. “I just don’t know.”

Ryan nodded as he tried to pretend as though he didn’t see Jim peering at him through the kitchen with Pam right behind him.

"I think this is really gonna help," Jim told him later as he pulled Ryan away from his desk to the kitchen area. Ryan paused his snapping as Jim placed a hand on his arm and moved ahead of him, "If you can just hold up here one second. 

"Hey, guys, just a quick announcement," Jim called over to their co-workers in the main part of the office. "If I could have everyone's attention."

Jim turned around to Ryan, "I just figured you needed a place where you could concentrate and not be bothered by bothering people."

Ryan nodded attentively but slightly confused, "Okay."

"Let me show you what I mean." Jim opened the storage closet to reveal a desk complete with a computer and phone, "Your new office. How great is that? For a job well done. Well... not done."

Ryan looked around him, "I will, uh, I will do my work right now," Ryan promised him, "I will stay late tonight-"

"Right."

Ryan looked up at him, "Um, I'm very sorry about everything-"

Jim laughed, almost tauntingly. "You're a good kid," he said, patting him on the shoulder, gently pushing him forward. "You know what, it gets bigger once you're in there. Enjoy it."

Ryan looked around the space when suddenly the door was shut behind him. "Is there internet?" Ryan called out after a moment.

He wasn’t even that mad when Jim tossed him into the closet. It _was_ a pretty big inconvenience, but granted, it beat having to spend more time around Kelly than absolutely necessary. In fact, in the short time where he avoided his closet space, it led him to an interesting discovery: in the copier tray, there was a manuscript.

 _My Diabolical Plan_ _by Dwight K. Schrute_

Ryan sat on what to do with the manuscript for a couple of days before approaching Dwight at closing time after Jim and Pam left.

“How’s it going? Good day?” Ryan asked quickly as he approached Dwight.

“Not now, Temp,” Dwight sighed.

Ryan took Phyllis’s abandoned chair anyway and pulled it over, “Um, okay. So, um, listen.” He sat down, “I know about your diabolical plan.”

Dwight huffed in feigned innocence, “What? Diabolical plan? I wouldn’t even know how to begin a dia…”

Ryan showed him the manuscript. “I found a copy of it in the copier tray.”

“So what do you want?” Dwight asked.

“I want the same thing you want,” Ryan told him. “I want to take Jim Halpert down.”

Dwight looked at him skeptically.

“I want in,” Ryan repeated.

Dwight thought about it for a moment before extending his hand to Ryan, who shook it.

Ryan had no ill will or intentions toward Jim, but just because he was in love with the guy didn’t mean he couldn't mess around with him a bit or knock him down a few pegs.

When Ryan first decides that he’s in love with Jim, he doesn’t care anymore about how unattainable he is. Ryan instead settles for the game of cat and mouse that is enough to satisfy him then.

**Notes for the Chapter:**

> Episodes Referenced:  
> The Carpet  
> Shareholder Meeting  
> Scott's Tots


	4. Pam Beesly

4\. The first time Ryan figures out he’s in love with Pam Beesly, it’s when they’re working together at the Michael Scott Paper Company.

Which is obviously not the first time he had attempted to ask her out.

They were in their little walk-in closet of a company, drained after a day of cold calls and bickering incessantly with one another. (He didn’t _actually_ think she was only a New York six. He kind of just said that to throw his buddy off the scent. Pam was too humble for that stuff anyway. You couldn’t limit describing her to how good-looking she was in Scranton or New York terms.)

Michael walked back into the room after enduring a depressingly uneventful pancake luncheon. He sat down solemnly, “I once had a dream that I was eating a peanut butter and tuna fish sandwich. And… let me tell you something, it was delicious. So the next day I decided to make that sandwich. And in real life it is disgusting.” The office’s phone started ringing, cutting off Michael’s seemingly pointless analog. “It is a disgusting sandwich,” Michael continued anyway and the phone rang again. 

Ryan and Pam exchanged a look.

“And the reason I tell you this story…” 

_Ring._

Michael shook his head in submission, “Pick up the phone. Just--”

Ryan watched as Pam reluctantly did so. “Dunder Mif--” she sighed at the force of habit. “Michael Scott Paper Company, this is Pam.” After a pause, she looked up, almost alarmed, “Oh, hi, Russell from the pancake luncheon. How are you? Well, we’d like to do business with you too.”

Ryan watched as Michael suddenly perked up.

“How can I make that happen?” Pam asked and Ryan gave her an encouraging thumbs up. 

Ryan motioned his hands supportingly upon seeing her struggle, “Keep going,” he whispered.

“Don’t tell him we have free delivery,” Michael whisper-shouted.

Pam covered the speaker of the phone, panicked and whispered, “We already offered free delivery.”

Michael waved his hand dismissively, “They don’t know that.”

“Um, I can offer you free delivery on any order that you place today,” Pam told the potential client.

Ryan’s attention went from Pam to Michael as the boss stood up abruptly from his desk and banged into the copier, “Ow! God!” He hit the table too, but Ryan steadied it before rushing to Pam’s side as well.

“Okay. Twenty boxes?” Ryan reached over to Pam’s arms to look over the form before she ushered him out of her way. “I can do twenty boxes at forty-three dollars a box.”

Ryan looked over her shoulder this time and stood up straight, nodding to Michael. 

“Great,” Pam said happily.

“Write it down,” Ryan urged in a hushed voice.

“Give him a guarantee,” Michael whispered.

Pam covered the speaker again, “A guarantee of what?”

“Just say the word,” he advised.

“And I guarantee… that you will be satisfied,” Pam said, her voice level and confident despite the unsureness. “‘Cause your satisfaction is our guarantee. We guarantee it.”

Michael nodded, proudly.

“We look forward to doing business with you too,” Pam smiled brightly. “Thank you, Russell.”

“Yes!” Michael exclaimed upon Pam hanging up.

“I made a sale!” Pam declared, beaming with pride.

“You did!” Michael beamed.

Ryan shouted out of enthusiasm, a sudden smile forming on his once neutral face. Michael and Pam hugged, thrilled at the strides that Pam and their company were already making. Pam turned to face Ryan and once Michael had released her, she quickly moved to him to give him an excited side-hug. 

Ryan embraced her back with a wide smile, “We did it! She did it!”

“Yeah!” Michael repeated as he and Ryan did a little dance while Pam jumped, all full of energy.

Ryan’s a little dizzy from the adrenaline rush of all the excitement and good energy in the room when he thinks fleetingly that he might be smitten with Pam. He doesn’t think it to be love or something it’s not. He’s content with how easy things are between them now that the tension has eased. He thinks briefly that not being her friend first is what messed up his relationship with Kelly. Ryan decides that he’s going to focus on growing a good friendship with Pam in hopes of gaining a friend rather than an enemy this time.

The feeling comes back the day the company’s going under. He and Michael are sitting on the floor of their closet when Pam comes back.

“Did I ever tell you about the day that Steve Martin died?” Michael asked them.

Pam was leaning against the wall behind him. He doesn’t see her, but he hears her when she says, “Steve Martin’s not dead, Michael.”

“I know,” Michael admitted, “But I always thought that the day that he died would be the worst day of my life. And I was wrong. It’s this.”

Pam moved from the wall to Michael’s left and suddenly Ryan shifts and pays attention.

“You want to hear something sad?” she asked them solemnly.

“I would love that,” Michael replied.

“So Jim and I are getting married and the wedding’s really expensive, so I tried to get a job on the weekends to earn extra money. I applied to Old Navy, Target, and Wal-Mart. None of ‘em called me back. Not even for an interview.”

Ryan thought that was absolutely ridiculous. Pam was the best receptionist that Dunder Mifflin’s ever had and the best salesperson at this company and Ryan damn well knew it. Those companies should be tripping over themselves _just_ to get an interview with her.

But something nagged at him as well. He opened his mouth in anticipation and managed to force the words out. “I never went to Thailand,” he admitted, feeling a prick of shame and anxiety that he couldn’t quite explain.

Michael looked at him in shock. Pam merely looked mildly surprised, “Really?”

He kept his head down, “I went to Fort Lauderdale.”

“Was it nice?” Michael asked, either out of sympathy or genuine obliviousness.

“Yeah, it was amazing,” Ryan replied, softly and facetiously. “There was a great Pad Thai place, though.”

They continued to sit there and talk. Eventually, Michael moved back to his desk and Ryan shifted over to sit closer to Pam. “I’m sorry about those stores,” he tells her, finally managing to look her in the eye after admitting to Thailand.

“It’s okay,” she replies with a shrug, but she seemed to appreciate the gesture. “I’m sorry about Thailand.”

He gives her a sad smile, “It’s okay.” 

They sat in silence for a bit. Ryan noticed Pam open her mouth in a similar way that he had before his confession: anxiously and unsure.

“I didn’t leave to get away from Kelly, if that’s what you’re thinking,” he says before she can ask. He licked his lips like he always does before saying, “I… I was at rehab.”

“Oh,” Pam gaped. “Are you…?”

“Yeah,” Ryan replied with a sharp nod. He smiled with a little bit of pride, “I’m better now.”

She smiled back. It’s a similar exchange to the one they had when Pam got their first client, one prideful in their own accomplishments and the other proud of them. “I’m really happy for you, Ryan.”

“Thanks,” he replied, another smile pulling at his lips.

Pam scooted closer to Ryan to give him a supportive side hug. He wraps his left arm around her shoulder to return it. He doesn’t ignore the little _ping_ in his chest when he does.

Eventually, Jim knocked on the door of their quaint closet before opening it like the nice guy that he is. “Hey, can I talk to you guys for a second?”

Michael shakes his head, “We’re not hiring, Jim.”

“Actually here for something else,” Jim replied.

“Listen, I can’t make you laugh right now,” Michael pushed.

“You know I love a good guessing game,” Jim replied facetiously, “But why don’t I just tell you what I’m here for? Turns out you guys have made a pretty big dent in the Dunder Mifflin sales.”

“Oh, that’s nice,” Ryan said, preoccupied with the jar of cheese puffs.

“David Wallace has asked me to come down here and see if you would be interested in Dunder Mifflin buying you out,” Jim continued.

“Seriously?” Pam asked skeptically. Ryan perked up in his seat behind her. “Are you being serious?”

“He’s bluffing, Pam,” Ryan warned her, mouth full of cheese puffs and pointing accusingly at Jim.

Jim quickly cut off Michael’s every attempt to form a sentence. “See, I’m here to learn as little information as possible. All I really need to hear is if your _incredibly successful_ company would be receptive to a buyout.”

It’s not long before Jim disregards Ryan’s “maybe” out of Michael and Pam’s “yeses” and he leaves.

Ryan’s not sure about how he feels about the change. He just knows that it was nice (spare anxiety-inducing) when he and Pam have to babysit Michael and make sure he keeps his mouth shut about them being broke and it’s good to have his old job back. Everything else he can figure out later.

When Ryan first decides that he’s in love with Pam Beesly, he knows that this time he _really_ can’t have her. The thing is that at that point, he didn’t even realise that he was in love with her fiancé too.

**Notes for the Chapter:**

> Episodes Referenced:  
> Michael Scott Paper Company  
> Broke


	5. Oscar Martinez

5\. The first time Ryan discovers another part of his identity, Oscar’s there to help him find it.

Oscar had opened the door to Ryan’s closet one day and said almost accusingly, “How?”

Ryan met his eyes unamused and not in the mood for puzzles. “What, Oscar?”

Oscar gave him a sort of dumbfounded look like he hadn’t thought that far ahead, and even if he did, all that planning had gone out of his head at that moment. “How do you know what a vibrator is?” he said instead, even though that was only a _part_ of what he had wanted to say.

“Because I’m not a child,” Ryan deadpanned, turning to return to his ‘work.’

“I know you’re not! It’s just--how do I put this?” Oscar pondered in frustration. “It’s just been bugging me. First, you’re certain that Robert Lipton is gay and then there’s the vibrator thing. _Then_ you seem a lot more comfortable at that gay bar than any of our other coworkers and there was that weird episode at Robert California’s party.”

Ryan turned back around, “What are you implying, Oscar?”

“I don’t know,” Oscar admitted. “I was hoping you could explain all of _that_ to me.”

“Did it ever occur to you that I might just be comfortable with my own masculinity that all of those things don’t bother me?” Ryan asked. 

Oscar gaped at him for a moment, unsure of how to respond or react.

“I’m _joking_ ,” Ryan finally said, lightening up a bit. “I wore those weird scarves and sweaters for nearly a year, of _course_ I’m not straight.”

“I--I didn’t want to make any assumptions,” Oscar fumbled. “Besides, you were going through that whole artistic-hipster thing and I thought that was a part of the aesthetic.”

“I’m _bisexual_ , Oscar,” Ryan clarified. “Does that clear things up?”

“Yes, I suppose it does.” Oscar quickly added, “However, I am worried that you might be a walking stereotype.”

“‘A walking stereotype’?” Ryan repeated. “Is this because of the scarves-sweaters-suspenders things?”

“No, no, not at all.” Oscar glanced over at the table outside. “Do you mind--?”

Ryan followed his gaze, “Oh no, not at all.”

Ryan closed the door of his closet workspace and sat with Oscar at the table next to the refrigerator. 

“I’m worried that your habit of infidelity might be influenced by negative stereotyping of bisexuality,” Oscar clarified. “It’s a very common, but untrue assumption that bisexual people are more likely to cheat on their partner just because they have more attraction options-”

“Oh no, it’s not that,” Ryan interrupted.

“Pardon me?”

“Look, man: I don’t cheat on Kelly sometimes because I’m bisexual or because some non-bi people push the stereotype that we’re unloyal,” Ryan explained.

“Then why do you do it?” Oscar asked.

“Kelly’s great; we have some good moments despite the fact that we’re kind of manipulative of each other,” Ryan elaborated. “But from day one she’s had this whole idea in her mind that the two of us are going to get married, have kids, and have this perfect little white-picket-fence life and I just… that’s not what _I_ want. Manipulation aside, I think that Kelly and I would probably just be better off as friends. I don’t feel the same way about dating as I did before. I’m not in it to ‘just have fun’ with no strings attached. I might actually want strings; I just don’t think I’m built to want romantic love from just one person.”

Oscar took a moment to let himself and Ryan regain their thoughts before speaking. “I see. That certainly is a loaded thought process.”

Ryan only nodded.

Oscar took a deep breath, “Ryan, have you ever heard of the term ‘polyamorous’?”

“Is that like ‘polygomy’?”

“Not at all,” Oscar explained. “Polyamorous is the identification that some people in the LGBTQ community use to describe the practice of engaging in more than one romantic and/or sexual relationships with the consent of all the people involved. I don’t know much about polyamory myself, but I am sure that the feeling of being polyamorous comes just as naturally as being bisexual does.”

Ryan nodded, intrigued. “So, how does that work?”

“From my understanding, it can work in a variety of different ways,” Oscar continued. “I would say that the two most common examples are three people who are all dating one another without excluding each other and the other being a consensual open relationship. Sort of like… if you and Kelly were polyamorous, you could date… Jim, for example if he and Pam were polyamorous. As long as Kelly knows and Pam knows, and Jim and you know about your respective girlfriends, it would be fine.”

“Seems complicated,” Ryan commented. The corners of his mouth turned up, “But fun. It sounds pretty honest, which is cool and different.”

“So,” Oscar posed, “What do you think?”

“I like it,” Ryan admitted. “I like it a lot. It sounds… right. Not just morally, but it makes me feel a little more whole, if that makes sense. I don’t think I’d be able to do that while I’m still dating Kelly, but maybe someday I’ll be able to. Yeah… I think I’d like that,” Ryan nodded to himself and smiled lightly before shifting his focus back to Oscar. “Thank you so much, Oscar.”

Oscar smiled, “Hey, anytime. I actually really enjoyed talking to you. I am so sorry for ambushing you earlier.”

“No worries, man,” Ryan said, a smile still tugging at his lips. “We should do this again sometime. I’d be really interested in hearing more about this whole thing and getting the chance to talk to you more. We don’t really see each other around the office as much as we do other people.”

“I’d like that,” Oscar agreed, grinning. “And I’m sure there’s plenty you could teach me as a younger person of the community.”

Oscar and Ryan sat comfortably in silence for another moment before returning to their respective jobs with plans to hang out on the weekend.

When Ryan first makes the decision that he believes he’s polyamorous, he does not repress or censor that part of himself. He merely waits for the day when he can fully embrace it.

**Notes for the Chapter:**

> Episodes Referenced:  
> Search Committee: Part 1  
> The Incentive  
> Trivia  
> Pool Party


	6. Ryan Howard

+1. When Ryan Howard first realizes what a mess he has made of his life, he wakes up panicked and cold next to Kelly Kapoor.

Light shines through the blinds of the hotel room and heat from Kelly’s warm body reflects off of her, but he lays there, undeniably cold. Kelly still sleeps soundly beside him when he testingly shifts and sits up. Ryan sits and stares at the wall in front of him for a while until he finally decides that he needs to get up or else he’ll drive himself mad.

He puts his clothes back on and sits at the small table that the hotel room has to offer. He thinks with bittersweet humor that it reminds him of the kitchen table at Dunder Mifflin.

He’ll probably never see that again.

Ryan realises with a painful afterthought how much of his life he’ll have to give up for this. Kelly and he never talked about what they were doing, they just ran from Dwight and Angela’s wedding to this hotel room and that was that.

Kelly had ditched her fiancé for him, which probably meant that she would have to avoid contact with her parents and--did that mean he’d have to cut off his mom too? She was the only family who had ever stayed with him through thick and thin; how could he just abandon her like tha--

_Oh god._

Ryan’s heat clenched in sudden, indescribable panic and his breathing grew labored as if he was back at Michael’s ‘Rabies Awareness Fun Run Race.’ 

He had left Drake. He could have killed him and then he just _abandoned_ him. The one person in this world that he was supposed to be there for like his mother was for him and he just _left_ him without a second thought. Ryan lowered his head and gripped it tightly with his hands.

“Ryan?” Kelly called, sitting up in bed. “What’s wrong?”

“Kelly…” Ryan looked up with a pained look. “We need to talk.”

She looked at him confused, but slipped on a robe and sat across from him at the table anyway. It was too early for her to argue.

“Kelly, I don’t think we thought this through. Like, _really_ thought this through,” Ryan said.

“But--”

“No, Kelly,” Ryan put his hand up to stop her. “I like you a lot. I always have and always will. But we’re not okay. Not together at least. We’re both so manipulative and self-destructive that our love is beyond repair. It’s time that you realize that Romeo and Juliet isn’t the love story you thought it was. It’s time for me to learn how to grow up too.”

Kelly sat there silently, unacknowledging of his words.

“I think that you deserve the world, Kelly,” Ryan continued, sincerely. “You have so much to offer it. You deserve to have that white-picket-fence life with a loving husband and the kids that you always wanted. I mean it. I can’t give that to you, Kelly. I can’t commit the way you want me to and it’s not fair to either of us.”

Kelly’s eyes welled with tears; he couldn’t tell what was happening in her brain. “I thought you said that you had ‘finally mastered commitment.’”

“I was wrong,” Ryan admitted. “Kelly, I said that because I thought it was true. But in the process of thinking I had finally been able to commit to _you_ , I had ran away from the one person I was _never_ supposed to leave.”

“Drake,” Kelly spoke, barely above a whisper.

Ryan nodded, “That’s right. Kelly, how can I commit to you if I couldn’t even commit to him?”

Kelly looked him in the eye and sniffled. She gave him a sad smile, “I think that’s the first time you’ve ever asked me a sincere question.”

He gave her a sad little laugh in return, “I think you’re right.”

She nodded to herself, “You have to make things right now, don’t you?”

“I do,” Ryan nodded his head in agreement, “And so do you. Ravi’s a really good guy, Kelly, and he’s really good to you. Your parents like him a lot and I think that you do too. I’m brave enough to admit that now. You should go to him. And stay with him this time, okay? If anyone can give you the life you deserve, it’s him.”

Kelly nodded her head again quickly with a tearful “Okay.”

Ryan lowered his head and stood up, beginning to take his leave.

“And what about you?” Kelly asked. “How are you going to find Drake?”

Ryan turned around to face her. “I know some people that will help me get him back. If anyone would help me, it’s them.”

“Good luck.”

“Thanks. And, Kelly?”

“Yes, Ryan?”

He fumbled, “Maybe someday, if you’re up to it, Ravi and your kids could play with Drake.”

Kelly smiled at him, a bit brighter. “I’d like that.”

“Yeah,” Ryan gave her a closed-lipped smile, “Me too.”

* * *

When Ryan knocks on the house’s door, he’s surprised at who answers.

“Ryan, hey,” Jim leaned his arm against the doorframe, seemingly equally as caught off guard. “What’s up?”

“I, uh, know you both must be very busy,” Ryan said, shifting uncomfortably, “but I was wondering if I could talk to you and Pam about something? It’s kind of important.”

Jim’s eyes darted from inside the house back to Ryan. “Yeah, of course. Did you want to come in or…?”

Ryan shook his head and he began to wring his hands nervously. “That’s okay. I’ll stay out here.”

Jim nodded. “I’ll be right back then,” he said before disappearing into the home.

It wasn’t long before Jim reappeared with Pam at his side.

“Hey, Ryan,” Pam greeted, giving him a small smile.

“Hey, Pam,” Ryan replied softly. Awkward silence followed as he stood there, sort of dumbfounded. Seeing them both again took him aback; he was surprised he had even made it this far.

“So, what’s this kind of important thing you wanted to talk to us about?” Jim asked, breaking the silence.

“Right. I, uh, just wanted to say first of all that I know that I haven’t always had the best relationship with either of you,” Ryan started. “And I am really, truly sorry for that. I admire you both so much and I’ve just been kind of lost for the majority of my adult life; I took that frustration out on the people around me and it wasn’t fair to anyone. I have had so many problems going on in my life for the past several years; I _myself_ have been problematic on so many levels and I… I just wanted to apologize.”

“I believe you,” Jim and Pam said softly in unison after a moment. They looked at each other in surprise.

Ryan was equally surprised. “Really?”

This time, it was Jim who spoke up. “Yeah. Ryan, before you went off to New York, you were a good kid.”

“And a good friend,” Pam added. “Ryan, before you went to work for corporate, I always enjoyed talking to you and despite how you might have felt about her, you were decent to Kelly. I caught a glimpse of that side of you coming back after you came back from Fort Lauderdale, but eventually the hunger for power that you got from working at corporate took over once again and you--”

“And I slipped,” Ryan finished, looking them in the eye. Ashamed of himself, he ran his hands through his hair and held his head, “I know. _God_ , I have been so terrible to you both -- and Kelly. I’m trying -- _really_ trying -- to get my life together and fix _this_ ,” he motioned to himself as well as the couple. “But I need your help.”

“How can we help you, Ryan?” Pam asked, taking his hands in hers.

“I made a bad decision at Dwight and Angela’s wedding yesterday,” Ryan told them. “I won’t call it a mistake because I consciously did it, but, Pam -- Jim -- I woke up this morning realizing what I had done and… I can’t believe I did it. I need to fix this myself, but I would like your help to help me get there.”

Pam looked him in the eyes with a warm sincerity, “What did you do, Ryan?”

Ryan couldn’t bear to look at her out of the guilt of what he had done. He had come to them knowing they were forgiving and kind enough to be the ones to help him, but he felt in that moment that he didn’t deserve for her to look at him that warmly. 

“I left Drake at the wedding,” Ryan said, barely above a whisper.

He half expected Jim to go off about how incredibly irresponsible that was and tell Pam not to waste their time when he was clearly beyond help. Instead, Jim placed a hand on Ryan’s arm with the type of delicateness one uses when handling something glass -- as if it could shatter at any moment. 

“It’s okay, Ryan,” he said instead. “We’ll help you get him back.”

Ryan looked up tearfully in shock, “Really? Do you know where he is?”

Pam nodded solemnly, “We saw Nellie Bertram leave with him.”

Ryan let out a frustrated sigh. There was no way he would be able to get his baby back from that woman.

Pam tightened her grip on his hands supportingly, “We’ll get him back, Ryan. I promise.”

Jim nodded and removed his hand from Ryan’s shoulder, “I’ll go get the keys.”

Jim already disappeared into the house when Ryan said, “Wait, seriously?”

“We’re not going to let you go get him all on your own,” Pam told him. “You’ve been alone for far too long, you need the support.”

Ryan nodded quietly, not about to question how she knew that.

Jim returned and jingled the keys in his hand, “I’ll drive you there, Ryan.”

Ryan let out a soft “okay” as Pam turned around to hold him in a side hug, “Let’s go then.”

* * *

Jim stopped the car at a place several blocks away from their own. Turning off the ignition, he turned to Ryan, “We’re here.”

Pam turned around as well, “Do you want us to come with you?”

Ryan shook his head, “No, that’s alright. You’ve already done plenty for me. I need to do this on my own.”

Pam nodded understanding, “Good luck.”

“We’ll be here when you’re done,” Jim told him and he looked like he meant it.

Ryan was taken aback, but his lips formed a small smile. “Okay, thanks.”

He opened the door to the backseat and exited, growing more unsure as he came closer to Nellie’s door. He knew without looking back that Jim and Pam were watching them intently from their car. Taking a deep breath, Ryan licked his lips and knocked on the door.

Nellie was quick to open the door. She looked him up and down, “Ryan. I’ve been expecting you.”

“Really?” Ryan asked, slightly surprised.

“No, not really,” she replied crassly. “I was actually expecting you _not_ to show up.”

Ryan’s heart sank; it appeared as though _everyone_ thought of him as irresponsible and uncommitting. He peered past her, “Is Drake here? Is he okay?”

“He’s fine,” Nellie bit back, blocking his view even more so. She seemed contemplative before she added, “No thanks to you.”

 _That_ stung. 

“Look, Nellie,” Ryan said, “I know you told the camera crew to come and find you if I wanted Drake back. Jim said--”

“Oh, yes, of course. You’re with the Halperts. Hello, Jim! Pam!” Nellie called, waving at them from the threshold. “I’m surprised to say the least; I thought they hated you.”

“So did I,” Ryan countered. “I guess we were both wrong.”

“No need to get snippy with me,” Nellie retorted. “You were lucky enough to find me this quickly. We were just getting ready to head to Europe.”

Ryan felt his face heat up. Who was she to think she could just steal his son just like she had taken Andy’s job and take him to another continent?

 _“She has no authority to just_ take _Drake. Especially to another continent,” Pam had assured him on the ride there. “She doesn’t have custody of him yet; guardianship of children is nothing at all like seeing a job opening and simply taking it. There’s a legal process and you already have that. The incident at the wedding more than likely won’t give her any ground to take him away from you: there’s nothing proving that this was a recurring incident and that it has or will ever happen again. She’s not even related to him in any way, so the likelihood that she’d even get any kind of custody over Drake is minimal at best.”_

“I…” Ryan’s mind went blank. He had thought he would just tell her about all the legal things Pam had told him about in the car and appeal to her logical side, if not threaten her with a lawsuit or something. But now… he wasn’t as sure. Ryan had spent so much of his life hiding behind one persona after the next: the temporary employee, the corporate hotshot, the carefree blond, the fake-deep artistic-hipster, and then whatever it was he had tried to be to keep Kelly. Maybe, just maybe, it was time for him to be genuine for one day.

“I want my son back, Nellie,” he told her. “I am holding myself accountable for my actions yesterday. It wasn’t fair to him or anyone else and it wasn’t right what I did. I don’t think that I ever thought about what I was doing until it was already done. But, Nellie, I’ll tell you this: I woke up this morning and realized what an absolute _mess_ I’ve made of my life and you don’t even know the _half_ of it. I made up my mind this morning that if I could get Drake back then I could fix my life, my relationships, and everything else I’ve screwed up. I could and _would_ do all of that if I could just get him back from _you_.

“I’m going to level with you, Nellie,” Ryan continued. Air was barely getting to his lungs, but he didn’t care; he had to finish this. “I don’t even know if Drake’s biologically mine. My last girlfriend got pregnant while we were together and once Drake was born, she split. Now, I may not know that, but what I _do_ know is that my mother was the only person who was consistently there for me. I don’t just want to leave him like his mother did; I want to be there for him like my mother was for me. Because goddamnit, Nellie,” Ryan choked out, tears beginning to spill down his cheek, “that boy inside your house is my _baby_. He’s the _only_ thing on this _Earth_ that may just really, truly be mine and I am the one that is supposed to _always_ be there for him. I won’t slip up again, I _promise_. Just, _please_ , Nellie. Let me have my son.”

Ryan stood there silently, allowing her time to take all of that in. His breathing was irregular and ragged; he bit back the sob that threatened to leave his throat and focus on regaining his breath.

“Ryan, that was… something,” Nellie said finally.

He nodded tearfully and watched with a sunken heart as she made her way back into her home.

With her gone, Ryan gasped for air and unwillingly let out the sob that had been stuck in his throat. He felt a clenching in his chest out of helplessness and hopelessness. He couldn’t bear to look back at Pam and Jim knowing that he had failed. _God_ , he was so _stupid_. If he had just stayed with him to begin with--

The door opened again. Nellie was back with Drake in her arms.

“You had me at ‘could and would,’” she told him with a smile as she handed Drake over to him. “Really. I did _not_ need to know the rest of that. But I am glad that you’ve come to your senses.”

Ryan took Drake in his arms carefully, almost unsure if this was even real. He let out another sob that he didn’t even realise that he was holding in. Ryan hugged his son tightly, but attentively and he cried into his tiny shoulder. He beamed, almost unconsciously, out of delight and relief.

“Thank you, Nellie,” Ryan sobbed, “Thank you so much.”

“Of course, Ryan,” Nellie replied, fondly stroking Drake’s head. “You have a lovely son; I trust you’ll take care of him this time.”

“I will. I swear that I will,” Ryan wept, holding Drake close.

“You better get a move on then,” Nellie indicated, pointing behind him. “I think that there are two fine people who are waiting to see you.”

Ryan’s teary eyes widened in confusion before he looked over his shoulder to see Pam and Jim outside of their car and waiting for them. Pam gave him a small wave.

He gave her a small smile in return and turned his head back to face Nellie, “What about you? Isn’t it your dream to adopt a child?”

“Well, yes, you’re right about that,” Nellie replied. She gave him a knowing smile, “But Robert California’s in Europe right now -- the gymnast mentoring thing didn’t really work out. If I play my cards right, I might be able to talk him into staying with me and… who knows?”

Ryan nodded, “Good luck with that.”

“Thank you, Ryan,” Nellie smiled. “Good luck with those two and this little one. I have a feeling that things are going to change for you.” She pet Drake’s head one last time, “And _you._ Take care of your father, will you?”

Ryan sniffled, “Thanks again, Nellie.”

Nellie nodded before closing the door once again.

Ryan gave Drake another squeeze before returning to Pam and Jim.

“So this is little Drake Howard,” Jim commented, petting the baby’s head.

Ryan nodded, still a little teary-eyed, “This is my boy.”

Drake in all of his cute, baby glory reached a hand out towards Pam. She looked to Ryan and he nodded before she took the tiny hand into her own.

“He’s adorable, Ryan,” Pam marveled, watching Drake’s small face fondly and intrigued.

Ryan beamed proudly, “Thanks.”

“So what are you going to do now?” Jim asked Ryan while Pam was still preoccupied with the fascinating baby.

“I, uh, hadn’t really thought that far,” Ryan admitted. “I guess I’ll just bring Drake back to my place. I’ll probably have to figure out a way to afford getting an actual house to raise him in, or maybe I could move in with my mother…”

“Why don’t you stay with us?” Jim proposed, seemingly completely serious.

“Seriously?” Ryan blurted in disbelief.

“Yeah, why not?” Jim insisted and Ryan really could not come up with a reason as to why not.

“That is,” Pam interjected, suddenly free from her baby fixation, “as long as you don’t mind moving to Austin.”

Ryan shrugged, “No, I actually don’t mind that at all. Are you guys sure you want to have me? I know I’ve been a handful and I really don’t want to impose.”

“It’s no trouble, Ryan,” Pam assured, placing a hand on his arm comfortingly.

“I could probably get you a job at Athleap, if you’re up to it,” Jim offered in addition.

“I… Wow,” Ryan gaped in utter disbelief. “Yeah, sure, that would be amazing.”

Jim and Pam exchanged a look and grinned. 

“Great, it’s settled then,” Pam said with a smile. “Welcome to the family, Ryan.”

Ryan used the palm of his free hand to wipe the tears welling in his eyes. He wasn’t sure how he could ever repay them for their kindness, but he and Drake went into Jim’s car and went home with them.

The first time Ryan Howard decides that he needs to take control of his life, he does. And in the process, he finds the best family that he could have ever hoped for.

**Notes for the Chapter:**

> If you've made it this far, I would just like to say, thanks for reading! If you enjoyed this fic, please leave a kudos and/or a comment so that I know! I really appreciate any constructive feedback, so just let me know so that if you liked something, I'll know to keep on doing it!


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